rubabel 0.1.0 → 0.1.1

data/rubabel.gemspec

@@ -0,0 +1,100 @@
+# Generated by jeweler
+# DO NOT EDIT THIS FILE DIRECTLY
+# Instead, edit Jeweler::Tasks in Rakefile, and run 'rake gemspec'
+# -*- encoding: utf-8 -*-
+
+Gem::Specification.new do |s|
+  s.name = "rubabel"
+  s.version = "0.1.1"
+
+  s.required_rubygems_version = Gem::Requirement.new(">= 0") if s.respond_to? :required_rubygems_version=
+  s.authors = ["John T. Prince"]
+  s.date = "2012-05-31"
+  s.description = "Ruby interface to the openbabel ruby bindings (or the openbabel gem).  The\ninterface attempts to be a ruby-ish analogue of pybel."
+  s.email = "jtprince@gmail.com"
+  s.executables = ["rubabel"]
+  s.extra_rdoc_files = [
+    "LICENSE",
+    "README.rdoc"
+  ]
+  s.files = [
+    ".document",
+    ".rspec",
+    "LICENSE",
+    "README.rdoc",
+    "Rakefile",
+    "VERSION",
+    "bin/rubabel",
+    "lib/rubabel.rb",
+    "lib/rubabel/atom.rb",
+    "lib/rubabel/bond.rb",
+    "lib/rubabel/fingerprint.rb",
+    "lib/rubabel/molecule.rb",
+    "lib/rubabel/molecule/fragmentable.rb",
+    "lib/rubabel/molecule_data.rb",
+    "lib/rubabel/pm.rb",
+    "lib/rubabel/smarts.rb",
+    "reference/OBConversion_methods.txt",
+    "reference/arity_method_list.txt",
+    "reference/arity_method_list_CLASS.txt",
+    "reference/atom_methods.txt",
+    "reference/bond_methods.txt",
+    "reference/get_methods.rb",
+    "reference/mol_methods.txt",
+    "rubabel.gemspec",
+    "spec/chemistry_toolkit_rosetta/README.txt",
+    "spec/chemistry_toolkit_rosetta/benzodiazepine.sdf.gz",
+    "spec/chemistry_toolkit_rosetta/benzodiazepine.smi.gz",
+    "spec/chemistry_toolkit_rosetta/chemistry_toolkit_rosetta_spec.rb",
+    "spec/chemistry_toolkit_rosetta/key/benzodiazepine_heavy_atom_counts.output.10.txt",
+    "spec/chemistry_toolkit_rosetta/key/benzodiazepine_ring_counts.output.10.txt",
+    "spec/chemistry_toolkit_rosetta/key/rule5.10.sdf",
+    "spec/rubabel/atom_spec.rb",
+    "spec/rubabel/bond_spec.rb",
+    "spec/rubabel/molecule/fragmentable_spec.rb",
+    "spec/rubabel/molecule_data_spec.rb",
+    "spec/rubabel/molecule_spec.rb",
+    "spec/rubabel_spec.rb",
+    "spec/spec_helper.rb",
+    "spec/testfiles/7-oxocholesterol-d7.mol",
+    "spec/testfiles/7-oxocholesterol-d7.sdf",
+    "spec/testfiles/Samples.sdf",
+    "spec/testfiles/Samples.sdf.gz",
+    "spec/testfiles/cholesterol.mol",
+    "spec/testfiles/cholesterol.sdf",
+    "spec/testfiles/two.sdf"
+  ]
+  s.homepage = "http://github.com/princelab/rubabel"
+  s.licenses = ["MIT"]
+  s.require_paths = ["lib"]
+  s.rubygems_version = "1.8.18"
+  s.summary = "Ruby interface to the OpenBabel ruby bindings similar to pybel"
+
+  if s.respond_to? :specification_version then
+    s.specification_version = 3
+
+    if Gem::Version.new(Gem::VERSION) >= Gem::Version.new('1.2.0') then
+      s.add_runtime_dependency(%q<openbabel>, ["~> 2.3.1.2"])
+      s.add_runtime_dependency(%q<commander>, ["~> 4.1.2"])
+      s.add_runtime_dependency(%q<andand>, ["~> 1.3.3"])
+      s.add_development_dependency(%q<rspec>, ["~> 2.8.0"])
+      s.add_development_dependency(%q<rdoc>, ["~> 3.12"])
+      s.add_development_dependency(%q<jeweler>, ["~> 1.8.3"])
+    else
+      s.add_dependency(%q<openbabel>, ["~> 2.3.1.2"])
+      s.add_dependency(%q<commander>, ["~> 4.1.2"])
+      s.add_dependency(%q<andand>, ["~> 1.3.3"])
+      s.add_dependency(%q<rspec>, ["~> 2.8.0"])
+      s.add_dependency(%q<rdoc>, ["~> 3.12"])
+      s.add_dependency(%q<jeweler>, ["~> 1.8.3"])
+    end
+  else
+    s.add_dependency(%q<openbabel>, ["~> 2.3.1.2"])
+    s.add_dependency(%q<commander>, ["~> 4.1.2"])
+    s.add_dependency(%q<andand>, ["~> 1.3.3"])
+    s.add_dependency(%q<rspec>, ["~> 2.8.0"])
+    s.add_dependency(%q<rdoc>, ["~> 3.12"])
+    s.add_dependency(%q<jeweler>, ["~> 1.8.3"])
+  end
+end
+

data/spec/chemistry_toolkit_rosetta/README.txt

@@ -0,0 +1 @@
+For space and sanity when running these tests, only the first 10 molecules are used.

data/spec/chemistry_toolkit_rosetta/chemistry_toolkit_rosetta_spec.rb

@@ -0,0 +1,225 @@
+require 'spec_helper'
+
+# http://ctr.wikia.com/wiki/Chemistry_Toolkit_Rosetta_Wiki
+
+
+# these are written as if the user is starting the project from scratch in the
+# style of the wiki.  We put the test files in the same folder as our specs so
+# that the code can be copied directly into the wiki
+
+# the code that should be copied is within the capture_stdout blocks
+
+module Kernel
+  def wiki_code(&block)
+    block.call
+  end
+
+  alias_method :wiki_code_capture_stdout, :capture_stdout
+end
+
+def unlink(file)
+  File.delete(file) if File.exist?(file)
+end
+
+describe 'Chemistry Toolkit Rosetta Wiki' do
+
+  before(:each) do
+    @orig_dir = Dir.pwd
+    @wiki_spec_dir = File.dirname(__FILE__)
+    Dir.chdir(@wiki_spec_dir)
+    @keydir =  @wiki_spec_dir + "/key"
+  end
+
+  after(:each) do 
+    Dir.chdir(@orig_dir)
+  end
+
+  it 'gets Heavy atom counts from an SD file' do
+    #http://ctr.wikia.com/wiki/Heavy_atom_counts_from_an_SD_file
+    output = wiki_code_capture_stdout do
+      require 'rubabel'
+      Rubabel.foreach("benzodiazepine.sdf.gz") {|mol| puts mol.ob.num_hvy_atoms }
+    end
+    output.should == IO.read( @keydir + "/" + "benzodiazepine_heavy_atom_counts.output.10.txt" )
+  end
+
+  it 'gets Ring counts in a SMILES file' do
+    # http://ctr.wikia.com/wiki/Ring_counts_in_a_SMILES_file
+    output = wiki_code_capture_stdout do
+      require 'rubabel'
+      Rubabel.foreach("benzodiazepine.sdf.gz") {|mol| puts mol.ob_sssr.size }
+    end
+    output.should == IO.read( @keydir + '/' + "benzodiazepine_ring_counts.output.10.txt" )
+  end
+
+  it 'Converts a SMILES string to canonical SMILES' do
+    # http://ctr.wikia.com/wiki/Convert_a_SMILES_string_to_canonical_SMILES
+    wiki_code do
+      require 'rubabel'
+      smiles = %w{CN2C(=O)N(C)C(=O)C1=C2N=CN1C CN1C=NC2=C1C(=O)N(C)C(=O)N2C}
+      cans = smiles.map {|smile| Rubabel[smile] }
+      fail unless cans.reduce(:==)
+    end
+  end
+
+  it 'Works with SD tag data' do
+    # http://ctr.wikia.com/wiki/Working_with_SD_tag_data
+    wiki_code do
+      require 'rubabel'
+      File.open("RULE5.sdf", 'w') do |out|
+        Rubabel.foreach("benzodiazepine.sdf.gz") do |mol|
+          mol.data["RULE5"] = 
+            if mol.data.key?('PUBCHEM_XLOGP3')
+              num_true = [
+                mol.data["PUBCHEM_CACTVS_HBOND_DONOR"].to_i <= 5,
+                mol.data["PUBCHEM_CACTVS_HBOND_ACCEPTOR"].to_i <= 10,
+                mol.data["PUBCHEM_MOLECULAR_WEIGHT"].to_f <= 500,
+                mol.data["PUBCHEM_XLOGP3"].to_f <= 5 
+              ].count(true)
+              if num_true >= 3 then "1" 
+              else "0"
+              end
+            else
+              "no logP"
+            end
+          out.print mol.write(:sdf)
+        end
+      end
+      # NOTE for wiki: This updates the #2 line of each molfile to mention "OpenBabel" and the current timestamp, as it ought to.
+    end
+    (lines_got, lines_exp) = ["RULE5.sdf", @keydir + "/rule5.10.sdf"].map do |file|
+      lines = IO.readlines(file).reject {|line| line =~ /OpenBabel/ }
+    end
+    lines_got[0,10].should == lines_exp[0,10]
+    unlink "RULE5.sdf"
+  end
+
+  it 'Detects and reports SMILES and SDF parsing errors' do
+    # http://ctr.wikia.com/wiki/Detect_and_report_SMILES_and_SDF_parsing_errors
+    wiki_code do
+      require 'rubabel'
+      File.open("log.txt", 'w') do |out|
+        %w(Q C1C).each do |smile|
+          Rubabel[smile] rescue out.puts "bad smiles #{smile}"
+        end
+      end
+      # note: error catching can only be performed with the from_string
+      # method at the moment.
+    end
+    IO.read("log.txt").should == "bad smiles Q\nbad smiles C1C\n"
+    puts "^^^^^ (ignore the above warning, part of spec) ^^^^^"
+    # TODO: implement error catching in file reading
+    # TODO: muffle the warning that Open Babel spits out on unmatched ring
+    # bonds.  Tried to capture stdout and stderr to no avail.
+    unlink("log.txt")
+  end
+
+  it 'Reports how many SD file records are within a certain molecular weight range' do
+    # http://ctr.wikia.com/wiki/Report_how_many_SD_file_records_are_within_a_certain_molecular_weight_range
+    output = wiki_code_capture_stdout do
+      require 'rubabel'
+      puts Rubabel.foreach("benzodiazepine.sdf.gz").count {|mol| (300..400) === mol.mol_wt }
+    end
+    output.should == "7\n"
+    # checked with large file and it came out to 3916, which is correct
+  end
+
+  it 'Converts SMILES file to SD file' do
+    # http://ctr.wikia.com/wiki/Convert_SMILES_file_to_SD_file
+    wiki_code do
+      require 'rubabel'
+      File.open("benzodiazepine.smi.sdf", 'w') do |out|
+        Rubabel.foreach("benzodiazepine.smi.gz") do |mol|
+          mol.make_3d!
+          out.print mol.write_string(:sdf)
+        end
+      end
+      # note: OpenBabel gets most stereochemistry correct.  When it cannot
+      # the particular atoms are noted in a message to stderr
+      # note: A minimal amount of optimization is performed in this routine
+      # (following pybel's make3D routine) so that the molecule doesn't make
+      # chemists reel.
+    end
+    unlink "benzodiazepine.smi.sdf"
+  end
+
+  it 'Reports the similarity between two structures' do
+    # http://ctr.wikia.com/wiki/Report_the_similarity_between_two_structures
+    output = wiki_code_capture_stdout do
+      require 'rubabel'
+      (mol1, mol2) = %w{CC(C)C=CCCCCC(=O)NCc1ccc(c(c1)OC)O COC1=C(C=CC(=C1)C=O)O}.map do |smile| 
+        Rubabel[smile]
+      end
+      puts mol1.tanimoto(mol2)
+    end
+    output.should == "0.36046511627906974\n"
+    # notes: reports similarity of 0.36046511627906974
+  end
+
+  it 'Finds the 10 nearest neighbors in a data set' do
+    # http://ctr.wikia.com/wiki/Find_the_10_nearest_neighbors_in_a_data_set
+    output = wiki_code_capture_stdout do
+      require 'rubabel'
+      fp1 = nil
+      comparisons = Rubabel.foreach("benzodiazepine.sdf.gz").map do |mol|
+        if fp1
+          [OpenBabel::OBFingerprint.tanimoto(fp1, mol.ob_fingerprint), mol.title]
+        else
+          (fp1 = mol.ob_fingerprint) && nil
+        end
+      end.compact
+      puts comparisons.sort.reverse[0,10].map {|v| "#{v[0].round(3)} #{v[1]}" }
+    end
+    output.should == "0.979 3016\n0.979 2997\n0.909 3369\n0.874 2809\n0.769 3299\n0.74 2802\n0.379 3261\n0.377 2118\n0.368 1963\n"
+    # notes: still need a first class fingerprint object so this cleaner
+    
+    # output when run on entire benzodiazepine.sdf.gz:
+    # 1.0 623918
+    # 1.0 450820
+    # 0.993 20351792
+    # 0.986 9862446
+    # 0.979 398658
+    # 0.979 398657
+    # 0.979 6452650
+    # 0.979 450830
+    # 0.979 44353759
+    # 0.979 3016
+
+    # this iterator method gives a segfault!! (not sure why)
+    #mol_iter = Rubabel.foreach("benzodiazepine.sdf.gz")
+    #fp1 = mol_iter.next.ob_fingerprint
+    #loop do
+    #  mol=mol_iter.next rescue break
+    #  comparisons << [OpenBabel::OBFingerprint.tanimoto(fp1, mol.ob_fingerprint).round(2), mol.title]
+    #end
+    #puts comparisons.sort.reverse.map {|pair| pair.join(" ") }
+  end
+
+  xit 'Depicts a compound as an image' do
+    # http://ctr.wikia.com/wiki/Depict_a_compound_as_an_image
+    wiki_code do
+      # still need to work on this!
+      #require 'rubabel'
+      #Rubabel["CN1C=NC2=C1C(=O)N(C(=O)N2C)C"].write_file("caffeine.svg")
+    end
+  end
+
+  xit 'Highlight a substructure in the depiction' do
+    smarts = "c1ccc2c(c1)C(=NCCN2)c3ccccc3"
+    mol = Rubabel.foreach("benzodiazepine.sdf.gz").find {|mol| mol.title == "3016" }
+    p OpenBabel::OBConversion.constants
+    p mol.obconv.get_options(OpenBabel::OBConversion.(:ALL))
+    #mol.write("hello.svg")
+  end
+
+
+end
+
+
+=begin
+  p OpenBabel::OBOp.methods - Object.methods
+  pgen = OpenBabel::OBOp.find_type("gen3D")
+  p pgen.methods - Object.new.methods
+  pgen.do(mol.ob)
+  out.print mol.write_string(:sdf)
+=end

data/spec/chemistry_toolkit_rosetta/key/benzodiazepine_heavy_atom_counts.output.10.txt

@@ -0,0 +1,10 @@
+21
+24
+22
+22
+22
+19
+20
+21
+25
+21

data/spec/chemistry_toolkit_rosetta/key/benzodiazepine_ring_counts.output.10.txt

@@ -0,0 +1,10 @@
+3
+4
+4
+3
+3
+3
+3
+4
+3
+3

data/spec/chemistry_toolkit_rosetta/key/rule5.10.sdf

@@ -0,0 +1,1924 @@
+1688
+ OpenBabel05151217162D
+
+ 33 35  0  0  0  0  0  0  0  0999 V2000
+    3.4148   -2.8597    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
+    8.1267   -2.2920    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
+    3.1645    2.8597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
+    2.9749    1.1769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
+    5.2219    1.1769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
+    4.0984   -0.2320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    3.1974    0.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    4.9994    0.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    4.5984    1.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    5.7812   -0.4216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    3.5984    1.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    4.1923   -1.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    2.3279   -0.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    2.0000    1.3994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    3.3362   -1.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    2.3977   -1.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    6.7121   -0.0562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    5.6322   -1.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    7.4939   -0.6797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    6.4140   -2.0339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    7.3449   -1.6685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    5.1570    2.2277    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
+    4.4605    2.5631    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
+    4.7539   -1.5319    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
+    1.7724   -0.0961    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
+    2.1380    2.0038    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
+    1.3955    1.5373    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
+    1.8620    0.7949    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
+    1.8841   -1.7581    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
+    6.8045    0.5568    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
+    5.0550   -1.6369    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
+    8.0711   -0.4532    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
+    6.3216   -2.6470    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
+  1 15  1  0  0  0  0
+  2 21  1  0  0  0  0
+  3 11  2  0  0  0  0
+  4  7  1  0  0  0  0
+  4 11  1  0  0  0  0
+  4 14  1  0  0  0  0
+  5  8  2  0  0  0  0
+  5  9  1  0  0  0  0
+  6  7  2  0  0  0  0
+  6  8  1  0  0  0  0
+  6 12  1  0  0  0  0
+  7 13  1  0  0  0  0
+  8 10  1  0  0  0  0
+  9 11  1  0  0  0  0
+  9 22  1  0  0  0  0
+  9 23  1  0  0  0  0
+ 10 17  2  0  0  0  0
+ 10 18  1  0  0  0  0
+ 12 15  2  0  0  0  0
+ 12 24  1  0  0  0  0
+ 13 16  2  0  0  0  0
+ 13 25  1  0  0  0  0
+ 14 26  1  0  0  0  0
+ 14 27  1  0  0  0  0
+ 14 28  1  0  0  0  0
+ 15 16  1  0  0  0  0
+ 16 29  1  0  0  0  0
+ 17 19  1  0  0  0  0
+ 17 30  1  0  0  0  0
+ 18 20  2  0  0  0  0
+ 18 31  1  0  0  0  0
+ 19 21  2  0  0  0  0
+ 19 32  1  0  0  0  0
+ 20 21  1  0  0  0  0
+ 20 33  1  0  0  0  0
+M  END
+>  <PUBCHEM_COMPOUND_CID>
+1688
+
+>  <PUBCHEM_COMPOUND_CANONICALIZED>
+1
+
+>  <PUBCHEM_CACTVS_COMPLEXITY>
+432
+
+>  <PUBCHEM_CACTVS_HBOND_ACCEPTOR>
+2
+
+>  <PUBCHEM_CACTVS_HBOND_DONOR>
+0
+
+>  <PUBCHEM_CACTVS_ROTATABLE_BOND>
+1
+
+>  <PUBCHEM_CACTVS_SUBSKEYS>
+AAADccB7IAAGAAAAAAAAAAAAAAAAAAAAAAAwYAAABAAAAAABQAAAHgIAAAAADArBmCQywIMAAACoAyVyVACCAAAhBwAIiACoZpgIYKLBk5GUIAhghgDIyAcQgMAOBABAIAACAAAIAIBAAAQAAAAAAAAAAA==
+
+>  <PUBCHEM_IUPAC_OPENEYE_NAME>
+7-chloro-5-(4-chlorophenyl)-1-methyl-3H-1,4-benzodiazepin-2-one
+
+>  <PUBCHEM_IUPAC_CAS_NAME>
+7-chloro-5-(4-chlorophenyl)-1-methyl-3H-1,4-benzodiazepin-2-one
+
+>  <PUBCHEM_IUPAC_NAME>
+7-chloro-5-(4-chlorophenyl)-1-methyl-3H-1,4-benzodiazepin-2-one
+
+>  <PUBCHEM_IUPAC_SYSTEMATIC_NAME>
+7-chloro-5-(4-chlorophenyl)-1-methyl-3H-1,4-benzodiazepin-2-one
+
+>  <PUBCHEM_IUPAC_TRADITIONAL_NAME>
+7-chloro-5-(4-chlorophenyl)-1-methyl-3H-1,4-benzodiazepin-2-one
+
+>  <PUBCHEM_NIST_INCHI>
+InChI=1S/C16H12Cl2N2O/c1-20-14-7-6-12(18)8-13(14)16(19-9-15(20)21)10-2-4-11(17)5-3-10/h2-8H,9H2,1H3
+
+>  <PUBCHEM_NIST_INCHIKEY>
+PUMYFTJOWAJIKF-UHFFFAOYSA-N
+
+>  <PUBCHEM_XLOGP3>
+3.8
+
+>  <PUBCHEM_EXACT_MASS>
+318.032668
+
+>  <PUBCHEM_MOLECULAR_FORMULA>
+C16H12Cl2N2O
+
+>  <PUBCHEM_MOLECULAR_WEIGHT>
+319.18528
+
+>  <PUBCHEM_OPENEYE_CAN_SMILES>
+CN1C(=O)CN=C(C2=C1C=CC(=C2)Cl)C3=CC=C(C=C3)Cl
+
+>  <PUBCHEM_OPENEYE_ISO_SMILES>
+CN1C(=O)CN=C(C2=C1C=CC(=C2)Cl)C3=CC=C(C=C3)Cl
+
+>  <PUBCHEM_CACTVS_TPSA>
+32.7
+
+>  <PUBCHEM_MONOISOTOPIC_WEIGHT>
+318.032668
+
+>  <PUBCHEM_TOTAL_CHARGE>
+0
+
+>  <PUBCHEM_HEAVY_ATOM_COUNT>
+21
+
+>  <PUBCHEM_ATOM_DEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_ATOM_UDEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_BOND_DEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_BOND_UDEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_ISOTOPIC_ATOM_COUNT>
+0
+
+>  <PUBCHEM_COMPONENT_COUNT>
+1
+
+>  <PUBCHEM_CACTVS_TAUTO_COUNT>
+1
+
+>  <PUBCHEM_COORDINATE_TYPE>
+1
+5
+255
+
+>  <PUBCHEM_BONDANNOTATIONS>
+10  17  8
+10  18  8
+12  15  8
+13  16  8
+15  16  8
+17  19  8
+18  20  8
+19  21  8
+20  21  8
+6  12  8
+6  7  8
+7  13  8
+
+>  <RULE5>
+1
+
+$$$$
+1963
+ OpenBabel05151217162D
+
+ 36 39  0  0  0  0  0  0  0  0999 V2000
+    2.0000    0.4189    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
+    6.4641    2.9350    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
+    5.4906   -3.5562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
+    5.8374   -0.9081    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
+    6.3374    1.2825    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
+    7.4235   -1.1945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
+    6.9517   -2.0695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
+    4.9365   -0.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    4.7139    0.5007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    6.7384   -0.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    5.3374    1.2825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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+    5.9734   -1.8928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    4.1839   -1.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    3.7234    0.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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+    5.2518   -2.5851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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+    3.5571    1.7460    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
+    5.3822    4.4230    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
+    2.8542    3.2055    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
+    3.7668    4.5441    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
+    5.0432   -3.9855    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
+  1 19  1  0  0  0  0
+  2 20  1  0  0  0  0
+  3 17  1  0  0  0  0
+  3 36  1  0  0  0  0
+  4  8  1  0  0  0  0
+  4 10  1  0  0  0  0
+  4 13  1  0  0  0  0
+  5 11  2  0  0  0  0
+  5 12  1  0  0  0  0
+  6  7  1  0  0  0  0
+  6 10  2  0  0  0  0
+  7 13  2  0  0  0  0
+  8  9  2  0  0  0  0
+  8 14  1  0  0  0  0
+  9 11  1  0  0  0  0
+  9 15  1  0  0  0  0
+ 10 12  1  0  0  0  0
+ 11 16  1  0  0  0  0
+ 12 25  1  0  0  0  0
+ 12 26  1  0  0  0  0
+ 13 17  1  0  0  0  0
+ 14 18  2  0  0  0  0
+ 14 27  1  0  0  0  0
+ 15 19  2  0  0  0  0
+ 15 28  1  0  0  0  0
+ 16 20  1  0  0  0  0
+ 16 21  2  0  0  0  0
+ 17 29  1  0  0  0  0
+ 17 30  1  0  0  0  0
+ 18 19  1  0  0  0  0
+ 18 31  1  0  0  0  0
+ 20 22  2  0  0  0  0
+ 21 23  1  0  0  0  0
+ 21 32  1  0  0  0  0
+ 22 24  1  0  0  0  0
+ 22 33  1  0  0  0  0
+ 23 24  2  0  0  0  0
+ 23 34  1  0  0  0  0
+ 24 35  1  0  0  0  0
+M  END
+>  <PUBCHEM_COMPOUND_CID>
+1963
+
+>  <PUBCHEM_COMPOUND_CANONICALIZED>
+1
+
+>  <PUBCHEM_CACTVS_COMPLEXITY>
+491
+
+>  <PUBCHEM_CACTVS_HBOND_ACCEPTOR>
+4
+
+>  <PUBCHEM_CACTVS_HBOND_DONOR>
+1
+
+>  <PUBCHEM_CACTVS_ROTATABLE_BOND>
+2
+
+>  <PUBCHEM_CACTVS_SUBSKEYS>
+AAADccB7oAAGAAAAAAAAAAAAAAAAAWAAAAAwYAAABAAAAACB0AAAHgIICAAADArhmyYx0IcMEgCiAyZiZASSgCshB6AdiAAwZpiKeKLBm5GUIAhgiALYyCcQgMAOAABAIAADAAAAAIBAAAYAAAAAAAAAAA==
+
+>  <PUBCHEM_IUPAC_OPENEYE_NAME>
+[8-chloro-6-(2-chlorophenyl)-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl]methanol
+
+>  <PUBCHEM_IUPAC_CAS_NAME>
+[8-chloro-6-(2-chlorophenyl)-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl]methanol
+
+>  <PUBCHEM_IUPAC_NAME>
+[8-chloro-6-(2-chlorophenyl)-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl]methanol
+
+>  <PUBCHEM_IUPAC_SYSTEMATIC_NAME>
+[8-chloro-6-(2-chlorophenyl)-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl]methanol
+
+>  <PUBCHEM_IUPAC_TRADITIONAL_NAME>
+[8-chloro-6-(2-chlorophenyl)-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl]methanol
+
+>  <PUBCHEM_NIST_INCHI>
+InChI=1S/C17H12Cl2N4O/c18-10-5-6-14-12(7-10)17(11-3-1-2-4-13(11)19)20-8-15-21-22-16(9-24)23(14)15/h1-7,24H,8-9H2
+
+>  <PUBCHEM_NIST_INCHIKEY>
+BHUYWUDMVCLHND-UHFFFAOYSA-N
+
+>  <PUBCHEM_XLOGP3>
+1.2
+
+>  <PUBCHEM_EXACT_MASS>
+358.038816
+
+>  <PUBCHEM_MOLECULAR_FORMULA>
+C17H12Cl2N4O
+
+>  <PUBCHEM_MOLECULAR_WEIGHT>
+359.20938
+
+>  <PUBCHEM_OPENEYE_CAN_SMILES>
+C1C2=NN=C(N2C3=C(C=C(C=C3)Cl)C(=N1)C4=CC=CC=C4Cl)CO
+
+>  <PUBCHEM_OPENEYE_ISO_SMILES>
+C1C2=NN=C(N2C3=C(C=C(C=C3)Cl)C(=N1)C4=CC=CC=C4Cl)CO
+
+>  <PUBCHEM_CACTVS_TPSA>
+63.3
+
+>  <PUBCHEM_MONOISOTOPIC_WEIGHT>
+358.038816
+
+>  <PUBCHEM_TOTAL_CHARGE>
+0
+
+>  <PUBCHEM_HEAVY_ATOM_COUNT>
+24
+
+>  <PUBCHEM_ATOM_DEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_ATOM_UDEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_BOND_DEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_BOND_UDEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_ISOTOPIC_ATOM_COUNT>
+0
+
+>  <PUBCHEM_COMPONENT_COUNT>
+1
+
+>  <PUBCHEM_CACTVS_TAUTO_COUNT>
+1
+
+>  <PUBCHEM_COORDINATE_TYPE>
+1
+5
+255
+
+>  <PUBCHEM_BONDANNOTATIONS>
+14  18  8
+15  19  8
+16  20  8
+16  21  8
+18  19  8
+20  22  8
+21  23  8
+22  24  8
+23  24  8
+4  10  8
+4  13  8
+6  10  8
+6  7  8
+7  13  8
+8  14  8
+8  9  8
+9  15  8
+
+>  <RULE5>
+1
+
+$$$$
+2118
+ OpenBabel05151217162D
+
+ 35 38  0  0  0  0  0  0  0  0999 V2000
+    2.0000   -0.2813    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
+    5.8374   -1.6083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
+    6.3374    0.5824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
+    7.4235   -1.8947    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
+    6.9517   -2.7696    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
+    4.9365   -1.1744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    4.7139   -0.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    6.7384   -1.1744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    5.3374    0.5824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    6.9609   -0.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    5.9734   -2.5930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    4.1839   -1.8945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    3.7234    0.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    4.9035    1.4834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    3.1862   -1.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    2.9544   -0.5797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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+    5.4669    2.3096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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+    3.5571    1.0458    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
+    6.0851    2.2633    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
+    2.8542    2.5054    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
+    5.3822    3.7228    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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+  1 16  1  0  0  0  0
+  2  6  1  0  0  0  0
+  2  8  1  0  0  0  0
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+  3  9  2  0  0  0  0
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+  4  5  1  0  0  0  0
+  4  8  2  0  0  0  0
+  5 11  2  0  0  0  0
+  6  7  2  0  0  0  0
+  6 12  1  0  0  0  0
+  7  9  1  0  0  0  0
+  7 13  1  0  0  0  0
+  8 10  1  0  0  0  0
+  9 14  1  0  0  0  0
+ 10 23  1  0  0  0  0
+ 10 24  1  0  0  0  0
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+ 12 15  2  0  0  0  0
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+ 13 26  1  0  0  0  0
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+ 15 16  1  0  0  0  0
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+ 17 28  1  0  0  0  0
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+ 20 22  2  0  0  0  0
+ 20 33  1  0  0  0  0
+ 21 22  1  0  0  0  0
+ 21 34  1  0  0  0  0
+ 22 35  1  0  0  0  0
+M  END
+>  <PUBCHEM_COMPOUND_CID>
+2118
+
+>  <PUBCHEM_COMPOUND_CANONICALIZED>
+1
+
+>  <PUBCHEM_CACTVS_COMPLEXITY>
+434
+
+>  <PUBCHEM_CACTVS_HBOND_ACCEPTOR>
+3
+
+>  <PUBCHEM_CACTVS_HBOND_DONOR>
+0
+
+>  <PUBCHEM_CACTVS_ROTATABLE_BOND>
+1
+
+>  <PUBCHEM_CACTVS_SUBSKEYS>
+AAADccB7gAAEAAAAAAAAAAAAAAAAAWAAAAAwYAAABAAAAACB0AAAHAIIAAAADArBGyQz0IcMEACiAyZiZACSgCshB6AdiAAwZpiIaKLBm5GUIAhgiALIyCcQgMAOAABAIAACAAAAAIBAAAQAAAAAAAAAAA==
+
+>  <PUBCHEM_IUPAC_OPENEYE_NAME>
+8-chloro-1-methyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine
+
+>  <PUBCHEM_IUPAC_CAS_NAME>
+8-chloro-1-methyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine
+
+>  <PUBCHEM_IUPAC_NAME>
+8-chloro-1-methyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine
+
+>  <PUBCHEM_IUPAC_SYSTEMATIC_NAME>
+8-chloro-1-methyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine
+
+>  <PUBCHEM_IUPAC_TRADITIONAL_NAME>
+8-chloro-1-methyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine
+
+>  <PUBCHEM_NIST_INCHI>
+InChI=1S/C17H13ClN4/c1-11-20-21-16-10-19-17(12-5-3-2-4-6-12)14-9-13(18)7-8-15(14)22(11)16/h2-9H,10H2,1H3
+
+>  <PUBCHEM_NIST_INCHIKEY>
+VREFGVBLTWBCJP-UHFFFAOYSA-N
+
+>  <PUBCHEM_XLOGP3>
+2.1
+
+>  <PUBCHEM_EXACT_MASS>
+308.082874
+
+>  <PUBCHEM_MOLECULAR_FORMULA>
+C17H13ClN4
+
+>  <PUBCHEM_MOLECULAR_WEIGHT>
+308.76492
+
+>  <PUBCHEM_OPENEYE_CAN_SMILES>
+CC1=NN=C2N1C3=C(C=C(C=C3)Cl)C(=NC2)C4=CC=CC=C4
+
+>  <PUBCHEM_OPENEYE_ISO_SMILES>
+CC1=NN=C2N1C3=C(C=C(C=C3)Cl)C(=NC2)C4=CC=CC=C4
+
+>  <PUBCHEM_CACTVS_TPSA>
+43.1
+
+>  <PUBCHEM_MONOISOTOPIC_WEIGHT>
+308.082874
+
+>  <PUBCHEM_TOTAL_CHARGE>
+0
+
+>  <PUBCHEM_HEAVY_ATOM_COUNT>
+22
+
+>  <PUBCHEM_ATOM_DEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_ATOM_UDEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_BOND_DEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_BOND_UDEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_ISOTOPIC_ATOM_COUNT>
+0
+
+>  <PUBCHEM_COMPONENT_COUNT>
+1
+
+>  <PUBCHEM_CACTVS_TAUTO_COUNT>
+1
+
+>  <PUBCHEM_COORDINATE_TYPE>
+1
+5
+255
+
+>  <PUBCHEM_BONDANNOTATIONS>
+12  15  8
+13  16  8
+14  18  8
+14  19  8
+15  16  8
+18  20  8
+19  21  8
+2  11  8
+2  8  8
+20  22  8
+21  22  8
+4  5  8
+4  8  8
+5  11  8
+6  12  8
+6  7  8
+7  13  8
+
+>  <RULE5>
+1
+
+$$$$
+2802
+ OpenBabel05151217162D
+
+ 32 34  0  0  0  0  0  0  0  0999 V2000
+    4.3734   -1.4925    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
+    2.8367    3.1429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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+    7.5017   -1.7719    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
+  1 18  1  0  0  0  0
+  2 16  2  0  0  0  0
+  3  7  1  0  0  0  0
+  4  7  2  0  0  0  0
+  5  9  1  0  0  0  0
+  5 16  1  0  0  0  0
+  5 24  1  0  0  0  0
+  6 10  2  0  0  0  0
+  6 14  1  0  0  0  0
+  7 15  1  0  0  0  0
+  8  9  2  0  0  0  0
+  8 10  1  0  0  0  0
+  8 12  1  0  0  0  0
+  9 13  1  0  0  0  0
+ 10 11  1  0  0  0  0
+ 11 18  1  0  0  0  0
+ 11 19  2  0  0  0  0
+ 12 15  2  0  0  0  0
+ 12 23  1  0  0  0  0
+ 13 17  2  0  0  0  0
+ 13 25  1  0  0  0  0
+ 14 16  1  0  0  0  0
+ 14 26  1  0  0  0  0
+ 14 27  1  0  0  0  0
+ 15 17  1  0  0  0  0
+ 17 28  1  0  0  0  0
+ 18 20  2  0  0  0  0
+ 19 21  1  0  0  0  0
+ 19 29  1  0  0  0  0
+ 20 22  1  0  0  0  0
+ 20 30  1  0  0  0  0
+ 21 22  2  0  0  0  0
+ 21 31  1  0  0  0  0
+ 22 32  1  0  0  0  0
+M  CHG  2   3  -1   7   1
+M  END
+>  <PUBCHEM_COMPOUND_CID>
+2802
+
+>  <PUBCHEM_COMPOUND_CANONICALIZED>
+1
+
+>  <PUBCHEM_CACTVS_COMPLEXITY>
+491
+
+>  <PUBCHEM_CACTVS_HBOND_ACCEPTOR>
+4
+
+>  <PUBCHEM_CACTVS_HBOND_DONOR>
+1
+
+>  <PUBCHEM_CACTVS_ROTATABLE_BOND>
+1
+
+>  <PUBCHEM_CACTVS_SUBSKEYS>
+AAADccBzMAAEAAAAAAAAAAAAAAAAAAAAAAAwYAAABAAAAAABQAAAHgIUAAAADArBmCQwwILQQACpAyVyVwCCAAAhBwAoiACgZpoIYKLBk5GUIAhglADIyAcQgMAOAACAQAADAAAAAQCAAAYAAAAAAAAAAA==
+
+>  <PUBCHEM_IUPAC_OPENEYE_NAME>
+5-(2-chlorophenyl)-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one
+
+>  <PUBCHEM_IUPAC_CAS_NAME>
+5-(2-chlorophenyl)-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one
+
+>  <PUBCHEM_IUPAC_NAME>
+5-(2-chlorophenyl)-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one
+
+>  <PUBCHEM_IUPAC_SYSTEMATIC_NAME>
+5-(2-chlorophenyl)-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one
+
+>  <PUBCHEM_IUPAC_TRADITIONAL_NAME>
+5-(2-chlorophenyl)-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one
+
+>  <PUBCHEM_NIST_INCHI>
+InChI=1S/C15H10ClN3O3/c16-12-4-2-1-3-10(12)15-11-7-9(19(21)22)5-6-13(11)18-14(20)8-17-15/h1-7H,8H2,(H,18,20)
+
+>  <PUBCHEM_NIST_INCHIKEY>
+DGBIGWXXNGSACT-UHFFFAOYSA-N
+
+>  <PUBCHEM_XLOGP3>
+2.4
+
+>  <PUBCHEM_EXACT_MASS>
+315.041069
+
+>  <PUBCHEM_MOLECULAR_FORMULA>
+C15H10ClN3O3
+
+>  <PUBCHEM_MOLECULAR_WEIGHT>
+315.7112
+
+>  <PUBCHEM_OPENEYE_CAN_SMILES>
+C1C(=O)NC2=C(C=C(C=C2)[N+](=O)[O-])C(=N1)C3=CC=CC=C3Cl
+
+>  <PUBCHEM_OPENEYE_ISO_SMILES>
+C1C(=O)NC2=C(C=C(C=C2)[N+](=O)[O-])C(=N1)C3=CC=CC=C3Cl
+
+>  <PUBCHEM_CACTVS_TPSA>
+84.6
+
+>  <PUBCHEM_MONOISOTOPIC_WEIGHT>
+315.041069
+
+>  <PUBCHEM_TOTAL_CHARGE>
+0
+
+>  <PUBCHEM_HEAVY_ATOM_COUNT>
+22
+
+>  <PUBCHEM_ATOM_DEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_ATOM_UDEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_BOND_DEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_BOND_UDEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_ISOTOPIC_ATOM_COUNT>
+0
+
+>  <PUBCHEM_COMPONENT_COUNT>
+1
+
+>  <PUBCHEM_CACTVS_TAUTO_COUNT>
+3
+
+>  <PUBCHEM_COORDINATE_TYPE>
+1
+5
+255
+
+>  <PUBCHEM_BONDANNOTATIONS>
+11  18  8
+11  19  8
+12  15  8
+13  17  8
+15  17  8
+18  20  8
+19  21  8
+20  22  8
+21  22  8
+8  12  8
+8  9  8
+9  13  8
+
+>  <RULE5>
+1
+
+$$$$
+2809
+ OpenBabel05151217162D
+
+ 33 35  0  0  1  0  0  0  0  0999 V2000
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+  1 15  1  0  0  0  0
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+  5  9  1  0  0  0  0
+  5 12  1  0  0  0  0
+  5 24  1  0  0  0  0
+  6  8  2  0  0  0  0
+  6 10  1  0  0  0  0
+  7  8  1  0  0  0  0
+  7  9  2  0  0  0  0
+  7 13  1  0  0  0  0
+  8 11  1  0  0  0  0
+  9 14  1  0  0  0  0
+ 10 12  1  0  0  0  0
+ 10 19  1  0  0  0  0
+ 10 23  1  0  0  0  0
+ 11 17  2  0  0  0  0
+ 11 18  1  0  0  0  0
+ 13 15  2  0  0  0  0
+ 13 25  1  0  0  0  0
+ 14 16  2  0  0  0  0
+ 14 26  1  0  0  0  0
+ 15 16  1  0  0  0  0
+ 16 27  1  0  0  0  0
+ 17 20  1  0  0  0  0
+ 17 28  1  0  0  0  0
+ 18 21  2  0  0  0  0
+ 18 29  1  0  0  0  0
+ 20 22  2  0  0  0  0
+ 20 30  1  0  0  0  0
+ 21 22  1  0  0  0  0
+ 21 31  1  0  0  0  0
+ 22 32  1  0  0  0  0
+M  END
+>  <PUBCHEM_COMPOUND_CID>
+2809
+
+>  <PUBCHEM_COMPOUND_CANONICALIZED>
+1
+
+>  <PUBCHEM_CACTVS_COMPLEXITY>
+488
+
+>  <PUBCHEM_CACTVS_HBOND_ACCEPTOR>
+4
+
+>  <PUBCHEM_CACTVS_HBOND_DONOR>
+2
+
+>  <PUBCHEM_CACTVS_ROTATABLE_BOND>
+2
+
+>  <PUBCHEM_CACTVS_SUBSKEYS>
+AAADccB7MAAEAAAAAAAAAAAAAAAAAAAAAAAwYAAABAAAAAABQAAAHgIQCAAADCrBmCQwyILAAgCoAyXyXACCAAAhBwAIiAGgZpgKYK7Jk5GUYAhitADIyAcQgMAOAABAIAACAAAAAIBAAAQAAAAAAAAAAA==
+
+>  <PUBCHEM_IUPAC_OPENEYE_NAME>
+7-chloro-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepine-3-carboxylic acid
+
+>  <PUBCHEM_IUPAC_CAS_NAME>
+7-chloro-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepine-3-carboxylic acid
+
+>  <PUBCHEM_IUPAC_NAME>
+7-chloro-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepine-3-carboxylic acid
+
+>  <PUBCHEM_IUPAC_SYSTEMATIC_NAME>
+7-chloro-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepine-3-carboxylic acid
+
+>  <PUBCHEM_IUPAC_TRADITIONAL_NAME>
+7-chloro-2-keto-5-phenyl-1,3-dihydro-1,4-benzodiazepine-3-carboxylic acid
+
+>  <PUBCHEM_NIST_INCHI>
+InChI=1S/C16H11ClN2O3/c17-10-6-7-12-11(8-10)13(9-4-2-1-3-5-9)19-14(16(21)22)15(20)18-12/h1-8,14H,(H,18,20)(H,21,22)
+
+>  <PUBCHEM_NIST_INCHIKEY>
+XDDJGVMJFWAHJX-UHFFFAOYSA-N
+
+>  <PUBCHEM_XLOGP3>
+3.3
+
+>  <PUBCHEM_EXACT_MASS>
+314.04582
+
+>  <PUBCHEM_MOLECULAR_FORMULA>
+C16H11ClN2O3
+
+>  <PUBCHEM_MOLECULAR_WEIGHT>
+314.72314
+
+>  <PUBCHEM_OPENEYE_CAN_SMILES>
+C1=CC=C(C=C1)C2=NC(C(=O)NC3=C2C=C(C=C3)Cl)C(=O)O
+
+>  <PUBCHEM_OPENEYE_ISO_SMILES>
+C1=CC=C(C=C1)C2=NC(C(=O)NC3=C2C=C(C=C3)Cl)C(=O)O
+
+>  <PUBCHEM_CACTVS_TPSA>
+78.8
+
+>  <PUBCHEM_MONOISOTOPIC_WEIGHT>
+314.04582
+
+>  <PUBCHEM_TOTAL_CHARGE>
+0
+
+>  <PUBCHEM_HEAVY_ATOM_COUNT>
+22
+
+>  <PUBCHEM_ATOM_DEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_ATOM_UDEF_STEREO_COUNT>
+1
+
+>  <PUBCHEM_BOND_DEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_BOND_UDEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_ISOTOPIC_ATOM_COUNT>
+0
+
+>  <PUBCHEM_COMPONENT_COUNT>
+1
+
+>  <PUBCHEM_CACTVS_TAUTO_COUNT>
+3
+
+>  <PUBCHEM_COORDINATE_TYPE>
+1
+5
+255
+
+>  <PUBCHEM_BONDANNOTATIONS>
+10  19  3
+11  17  8
+11  18  8
+13  15  8
+14  16  8
+15  16  8
+17  20  8
+18  21  8
+20  22  8
+21  22  8
+7  13  8
+7  9  8
+9  14  8
+
+>  <RULE5>
+1
+
+$$$$
+2997
+ OpenBabel05151217162D
+
+ 30 32  0  0  0  0  0  0  0  0999 V2000
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+ 19 30  1  0  0  0  0
+M  END
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+
+>  <PUBCHEM_COMPOUND_CANONICALIZED>
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+
+>  <PUBCHEM_IUPAC_OPENEYE_NAME>
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+
+>  <PUBCHEM_IUPAC_CAS_NAME>
+7-chloro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one
+
+>  <PUBCHEM_IUPAC_NAME>
+7-chloro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one
+
+>  <PUBCHEM_IUPAC_SYSTEMATIC_NAME>
+7-chloro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one
+
+>  <PUBCHEM_IUPAC_TRADITIONAL_NAME>
+7-chloro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one
+
+>  <PUBCHEM_NIST_INCHI>
+InChI=1S/C15H11ClN2O/c16-11-6-7-13-12(8-11)15(17-9-14(19)18-13)10-4-2-1-3-5-10/h1-8H,9H2,(H,18,19)
+
+>  <PUBCHEM_NIST_INCHIKEY>
+AKPLHCDWDRPJGD-UHFFFAOYSA-N
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+>  <PUBCHEM_XLOGP3>
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+>  <PUBCHEM_EXACT_MASS>
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+
+>  <PUBCHEM_MOLECULAR_FORMULA>
+C15H11ClN2O
+
+>  <PUBCHEM_MOLECULAR_WEIGHT>
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+
+>  <PUBCHEM_OPENEYE_CAN_SMILES>
+C1C(=O)NC2=C(C=C(C=C2)Cl)C(=N1)C3=CC=CC=C3
+
+>  <PUBCHEM_OPENEYE_ISO_SMILES>
+C1C(=O)NC2=C(C=C(C=C2)Cl)C(=N1)C3=CC=CC=C3
+
+>  <PUBCHEM_CACTVS_TPSA>
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+
+>  <PUBCHEM_MONOISOTOPIC_WEIGHT>
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+
+>  <PUBCHEM_TOTAL_CHARGE>
+0
+
+>  <PUBCHEM_HEAVY_ATOM_COUNT>
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+
+>  <PUBCHEM_ATOM_DEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_ATOM_UDEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_BOND_DEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_BOND_UDEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_ISOTOPIC_ATOM_COUNT>
+0
+
+>  <PUBCHEM_COMPONENT_COUNT>
+1
+
+>  <PUBCHEM_CACTVS_TAUTO_COUNT>
+3
+
+>  <PUBCHEM_COORDINATE_TYPE>
+1
+5
+255
+
+>  <PUBCHEM_BONDANNOTATIONS>
+11  14  8
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+17  19  8
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+5  7  8
+5  9  8
+7  11  8
+8  15  8
+8  16  8
+9  13  8
+
+>  <RULE5>
+1
+
+$$$$
+3016
+ OpenBabel05151217162D
+
+ 33 35  0  0  0  0  0  0  0  0999 V2000
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+ 20 33  1  0  0  0  0
+M  END
+>  <PUBCHEM_COMPOUND_CID>
+3016
+
+>  <PUBCHEM_COMPOUND_CANONICALIZED>
+1
+
+>  <PUBCHEM_CACTVS_COMPLEXITY>
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+>  <PUBCHEM_CACTVS_HBOND_ACCEPTOR>
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+
+>  <PUBCHEM_CACTVS_HBOND_DONOR>
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+>  <PUBCHEM_CACTVS_ROTATABLE_BOND>
+1
+
+>  <PUBCHEM_CACTVS_SUBSKEYS>
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+
+>  <PUBCHEM_IUPAC_OPENEYE_NAME>
+7-chloro-1-methyl-5-phenyl-3H-1,4-benzodiazepin-2-one
+
+>  <PUBCHEM_IUPAC_CAS_NAME>
+7-chloro-1-methyl-5-phenyl-3H-1,4-benzodiazepin-2-one
+
+>  <PUBCHEM_IUPAC_NAME>
+7-chloro-1-methyl-5-phenyl-3H-1,4-benzodiazepin-2-one
+
+>  <PUBCHEM_IUPAC_SYSTEMATIC_NAME>
+7-chloro-1-methyl-5-phenyl-3H-1,4-benzodiazepin-2-one
+
+>  <PUBCHEM_IUPAC_TRADITIONAL_NAME>
+7-chloro-1-methyl-5-phenyl-3H-1,4-benzodiazepin-2-one
+
+>  <PUBCHEM_NIST_INCHI>
+InChI=1S/C16H13ClN2O/c1-19-14-8-7-12(17)9-13(14)16(18-10-15(19)20)11-5-3-2-4-6-11/h2-9H,10H2,1H3
+
+>  <PUBCHEM_NIST_INCHIKEY>
+AAOVKJBEBIDNHE-UHFFFAOYSA-N
+
+>  <PUBCHEM_XLOGP3>
+3
+
+>  <PUBCHEM_EXACT_MASS>
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+
+>  <PUBCHEM_MOLECULAR_FORMULA>
+C16H13ClN2O
+
+>  <PUBCHEM_MOLECULAR_WEIGHT>
+284.74022
+
+>  <PUBCHEM_OPENEYE_CAN_SMILES>
+CN1C(=O)CN=C(C2=C1C=CC(=C2)Cl)C3=CC=CC=C3
+
+>  <PUBCHEM_OPENEYE_ISO_SMILES>
+CN1C(=O)CN=C(C2=C1C=CC(=C2)Cl)C3=CC=CC=C3
+
+>  <PUBCHEM_CACTVS_TPSA>
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+
+>  <PUBCHEM_MONOISOTOPIC_WEIGHT>
+284.071641
+
+>  <PUBCHEM_TOTAL_CHARGE>
+0
+
+>  <PUBCHEM_HEAVY_ATOM_COUNT>
+20
+
+>  <PUBCHEM_ATOM_DEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_ATOM_UDEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_BOND_DEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_BOND_UDEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_ISOTOPIC_ATOM_COUNT>
+0
+
+>  <PUBCHEM_COMPONENT_COUNT>
+1
+
+>  <PUBCHEM_CACTVS_TAUTO_COUNT>
+1
+
+>  <PUBCHEM_COORDINATE_TYPE>
+1
+5
+255
+
+>  <PUBCHEM_BONDANNOTATIONS>
+10  16  8
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+5  11  8
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+
+>  <RULE5>
+1
+
+$$$$
+3261
+ OpenBabel05151217162D
+
+ 32 35  0  0  0  0  0  0  0  0999 V2000
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+ 21 32  1  0  0  0  0
+M  END
+>  <PUBCHEM_COMPOUND_CID>
+3261
+
+>  <PUBCHEM_COMPOUND_CANONICALIZED>
+1
+
+>  <PUBCHEM_CACTVS_COMPLEXITY>
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+>  <PUBCHEM_CACTVS_HBOND_ACCEPTOR>
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+>  <PUBCHEM_CACTVS_HBOND_DONOR>
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+
+>  <PUBCHEM_IUPAC_OPENEYE_NAME>
+8-chloro-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine
+
+>  <PUBCHEM_IUPAC_CAS_NAME>
+8-chloro-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine
+
+>  <PUBCHEM_IUPAC_NAME>
+8-chloro-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine
+
+>  <PUBCHEM_IUPAC_SYSTEMATIC_NAME>
+8-chloro-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine
+
+>  <PUBCHEM_IUPAC_TRADITIONAL_NAME>
+8-chloro-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine
+
+>  <PUBCHEM_NIST_INCHI>
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+
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+>  <PUBCHEM_XLOGP3>
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+>  <PUBCHEM_EXACT_MASS>
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+>  <PUBCHEM_MOLECULAR_FORMULA>
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+
+>  <PUBCHEM_MOLECULAR_WEIGHT>
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+
+>  <PUBCHEM_OPENEYE_CAN_SMILES>
+C1C2=NN=CN2C3=C(C=C(C=C3)Cl)C(=N1)C4=CC=CC=C4
+
+>  <PUBCHEM_OPENEYE_ISO_SMILES>
+C1C2=NN=CN2C3=C(C=C(C=C3)Cl)C(=N1)C4=CC=CC=C4
+
+>  <PUBCHEM_CACTVS_TPSA>
+43.1
+
+>  <PUBCHEM_MONOISOTOPIC_WEIGHT>
+294.067224
+
+>  <PUBCHEM_TOTAL_CHARGE>
+0
+
+>  <PUBCHEM_HEAVY_ATOM_COUNT>
+21
+
+>  <PUBCHEM_ATOM_DEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_ATOM_UDEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_BOND_DEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_BOND_UDEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_ISOTOPIC_ATOM_COUNT>
+0
+
+>  <PUBCHEM_COMPONENT_COUNT>
+1
+
+>  <PUBCHEM_CACTVS_TAUTO_COUNT>
+1
+
+>  <PUBCHEM_COORDINATE_TYPE>
+1
+5
+255
+
+>  <PUBCHEM_BONDANNOTATIONS>
+11  17  8
+11  18  8
+12  15  8
+13  16  8
+15  16  8
+17  19  8
+18  20  8
+19  21  8
+2  14  8
+2  9  8
+20  21  8
+4  5  8
+4  9  8
+5  14  8
+6  12  8
+6  7  8
+7  13  8
+
+>  <RULE5>
+1
+
+$$$$
+3299
+ OpenBabel05151217162D
+
+ 39 41  0  0  1  0  0  0  0  0999 V2000
+    3.0869   -3.3849    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
+    4.3734   -2.3010    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
+    5.7016    2.4092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
+    2.8367    2.3344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
+    4.1411    3.1607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
+    2.6471    0.6516    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
+    4.8940    0.6516    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
+    3.7705   -0.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    4.6715   -0.3233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    4.2705    1.4335    0.0000 C   0  0  3  0  0  0  0  0  0  0  0  0
+    2.8696   -0.3233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    5.4533   -0.9468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    3.2705    1.4335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    3.8644   -1.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    2.0000   -0.8967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    4.7044    2.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    3.0083   -2.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    2.0698   -1.9360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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+    6.3842   -0.5814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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+    7.7432   -0.9784    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
+    7.5017   -2.5803    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
+    6.1973    3.9271    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
+    5.5387    3.4781    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
+    7.1791    2.7666    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
+    7.7510    3.4312    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
+    7.0864    4.0031    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
+  1 17  1  0  0  0  0
+  2 19  1  0  0  0  0
+  3 16  1  0  0  0  0
+  3 24  1  0  0  0  0
+  4 13  2  0  0  0  0
+  5 16  2  0  0  0  0
+  6 11  1  0  0  0  0
+  6 13  1  0  0  0  0
+  6 27  1  0  0  0  0
+  7  9  2  0  0  0  0
+  7 10  1  0  0  0  0
+  8  9  1  0  0  0  0
+  8 11  2  0  0  0  0
+  8 14  1  0  0  0  0
+  9 12  1  0  0  0  0
+ 10 13  1  0  0  0  0
+ 10 16  1  0  0  0  0
+ 10 26  1  0  0  0  0
+ 11 15  1  0  0  0  0
+ 12 19  1  0  0  0  0
+ 12 20  2  0  0  0  0
+ 14 17  2  0  0  0  0
+ 14 28  1  0  0  0  0
+ 15 18  2  0  0  0  0
+ 15 29  1  0  0  0  0
+ 17 18  1  0  0  0  0
+ 18 30  1  0  0  0  0
+ 19 21  2  0  0  0  0
+ 20 22  1  0  0  0  0
+ 20 31  1  0  0  0  0
+ 21 23  1  0  0  0  0
+ 21 32  1  0  0  0  0
+ 22 23  2  0  0  0  0
+ 22 33  1  0  0  0  0
+ 23 34  1  0  0  0  0
+ 24 25  1  0  0  0  0
+ 24 35  1  0  0  0  0
+ 24 36  1  0  0  0  0
+ 25 37  1  0  0  0  0
+ 25 38  1  0  0  0  0
+ 25 39  1  0  0  0  0
+M  END
+>  <PUBCHEM_COMPOUND_CID>
+3299
+
+>  <PUBCHEM_COMPOUND_CANONICALIZED>
+1
+
+>  <PUBCHEM_CACTVS_COMPLEXITY>
+556
+
+>  <PUBCHEM_CACTVS_HBOND_ACCEPTOR>
+5
+
+>  <PUBCHEM_CACTVS_HBOND_DONOR>
+1
+
+>  <PUBCHEM_CACTVS_ROTATABLE_BOND>
+4
+
+>  <PUBCHEM_CACTVS_SUBSKEYS>
+AAADccB7MQAEAAAAAAAAAAAAAAAAAAAAAAAwYAAABAAAAAABQAAAHwIQAAAADCrhmC4yyILABACoAyXyXACCAAAhBwAIiAGgZpgKYK7Jk5GXIAhitADIyAcQgMAOAABAIAACAAAAAIBAAAQAAAAAAAAAAA==
+
+>  <PUBCHEM_IUPAC_OPENEYE_NAME>
+ethyl 7-chloro-5-(2-fluorophenyl)-2-oxo-1,3-dihydro-1,4-benzodiazepine-3-carboxylate
+
+>  <PUBCHEM_IUPAC_CAS_NAME>
+7-chloro-5-(2-fluorophenyl)-2-oxo-1,3-dihydro-1,4-benzodiazepine-3-carboxylic acid ethyl ester
+
+>  <PUBCHEM_IUPAC_NAME>
+ethyl 7-chloro-5-(2-fluorophenyl)-2-oxo-1,3-dihydro-1,4-benzodiazepine-3-carboxylate
+
+>  <PUBCHEM_IUPAC_SYSTEMATIC_NAME>
+ethyl 7-chloro-5-(2-fluorophenyl)-2-oxo-1,3-dihydro-1,4-benzodiazepine-3-carboxylate
+
+>  <PUBCHEM_IUPAC_TRADITIONAL_NAME>
+7-chloro-5-(2-fluorophenyl)-2-keto-1,3-dihydro-1,4-benzodiazepine-3-carboxylic acid ethyl ester
+
+>  <PUBCHEM_NIST_INCHI>
+InChI=1S/C18H14ClFN2O3/c1-2-25-18(24)16-17(23)21-14-8-7-10(19)9-12(14)15(22-16)11-5-3-4-6-13(11)20/h3-9,16H,2H2,1H3,(H,21,23)
+
+>  <PUBCHEM_NIST_INCHIKEY>
+CUCHJCMWNFEYOM-UHFFFAOYSA-N
+
+>  <PUBCHEM_XLOGP3>
+2.9
+
+>  <PUBCHEM_EXACT_MASS>
+360.067698
+
+>  <PUBCHEM_MOLECULAR_FORMULA>
+C18H14ClFN2O3
+
+>  <PUBCHEM_MOLECULAR_WEIGHT>
+360.766763
+
+>  <PUBCHEM_OPENEYE_CAN_SMILES>
+CCOC(=O)C1C(=O)NC2=C(C=C(C=C2)Cl)C(=N1)C3=CC=CC=C3F
+
+>  <PUBCHEM_OPENEYE_ISO_SMILES>
+CCOC(=O)C1C(=O)NC2=C(C=C(C=C2)Cl)C(=N1)C3=CC=CC=C3F
+
+>  <PUBCHEM_CACTVS_TPSA>
+67.8
+
+>  <PUBCHEM_MONOISOTOPIC_WEIGHT>
+360.067698
+
+>  <PUBCHEM_TOTAL_CHARGE>
+0
+
+>  <PUBCHEM_HEAVY_ATOM_COUNT>
+25
+
+>  <PUBCHEM_ATOM_DEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_ATOM_UDEF_STEREO_COUNT>
+1
+
+>  <PUBCHEM_BOND_DEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_BOND_UDEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_ISOTOPIC_ATOM_COUNT>
+0
+
+>  <PUBCHEM_COMPONENT_COUNT>
+1
+
+>  <PUBCHEM_CACTVS_TAUTO_COUNT>
+3
+
+>  <PUBCHEM_COORDINATE_TYPE>
+1
+5
+255
+
+>  <PUBCHEM_BONDANNOTATIONS>
+10  16  3
+11  15  8
+12  19  8
+12  20  8
+14  17  8
+15  18  8
+17  18  8
+19  21  8
+20  22  8
+21  23  8
+22  23  8
+8  11  8
+8  14  8
+
+>  <RULE5>
+1
+
+$$$$
+3369
+ OpenBabel05151217162D
+
+ 33 35  0  0  0  0  0  0  0  0999 V2000
+    3.4148   -2.8597    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
+    4.7013   -1.7757    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
+    3.1645    2.8597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
+    2.9749    1.1769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
+    5.2219    1.1769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
+    4.0984   -0.2320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    3.1974    0.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    4.9994    0.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    4.5984    1.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    5.7812   -0.4216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    3.5984    1.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    4.1923   -1.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    2.3279   -0.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    2.0000    1.3994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
+    3.3362   -1.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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+    5.6322   -1.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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+    1.7724   -0.0961    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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+    8.0711   -0.4532    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
+    7.8296   -2.0551    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
+  1 15  1  0  0  0  0
+  2 17  1  0  0  0  0
+  3 11  2  0  0  0  0
+  4  7  1  0  0  0  0
+  4 11  1  0  0  0  0
+  4 14  1  0  0  0  0
+  5  8  2  0  0  0  0
+  5  9  1  0  0  0  0
+  6  7  2  0  0  0  0
+  6  8  1  0  0  0  0
+  6 12  1  0  0  0  0
+  7 13  1  0  0  0  0
+  8 10  1  0  0  0  0
+  9 11  1  0  0  0  0
+  9 22  1  0  0  0  0
+  9 23  1  0  0  0  0
+ 10 17  1  0  0  0  0
+ 10 18  2  0  0  0  0
+ 12 15  2  0  0  0  0
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+ 13 16  2  0  0  0  0
+ 13 25  1  0  0  0  0
+ 14 26  1  0  0  0  0
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+ 15 16  1  0  0  0  0
+ 16 29  1  0  0  0  0
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+ 18 20  1  0  0  0  0
+ 18 30  1  0  0  0  0
+ 19 21  1  0  0  0  0
+ 19 31  1  0  0  0  0
+ 20 21  2  0  0  0  0
+ 20 32  1  0  0  0  0
+ 21 33  1  0  0  0  0
+M  END
+>  <PUBCHEM_COMPOUND_CID>
+3369
+
+>  <PUBCHEM_COMPOUND_CANONICALIZED>
+1
+
+>  <PUBCHEM_CACTVS_COMPLEXITY>
+442
+
+>  <PUBCHEM_CACTVS_HBOND_ACCEPTOR>
+3
+
+>  <PUBCHEM_CACTVS_HBOND_DONOR>
+0
+
+>  <PUBCHEM_CACTVS_ROTATABLE_BOND>
+1
+
+>  <PUBCHEM_CACTVS_SUBSKEYS>
+AAADccB7IQAEAAAAAAAAAAAAAAAAAAAAAAAwYAAABAAAAAABQAAAHwIAAAAADArBmCwywIMAAACoAyVyVACCAAAhBwAIiACoZpgIYKLBk5GUIAhghgDIyAcQgMAOAABAIAACAAAAAIBAAAQAAAAAAAAAAA==
+
+>  <PUBCHEM_IUPAC_OPENEYE_NAME>
+7-chloro-5-(2-fluorophenyl)-1-methyl-3H-1,4-benzodiazepin-2-one
+
+>  <PUBCHEM_IUPAC_CAS_NAME>
+7-chloro-5-(2-fluorophenyl)-1-methyl-3H-1,4-benzodiazepin-2-one
+
+>  <PUBCHEM_IUPAC_NAME>
+7-chloro-5-(2-fluorophenyl)-1-methyl-3H-1,4-benzodiazepin-2-one
+
+>  <PUBCHEM_IUPAC_SYSTEMATIC_NAME>
+7-chloro-5-(2-fluorophenyl)-1-methyl-3H-1,4-benzodiazepin-2-one
+
+>  <PUBCHEM_IUPAC_TRADITIONAL_NAME>
+7-chloro-5-(2-fluorophenyl)-1-methyl-3H-1,4-benzodiazepin-2-one
+
+>  <PUBCHEM_NIST_INCHI>
+InChI=1S/C16H12ClFN2O/c1-20-14-7-6-10(17)8-12(14)16(19-9-15(20)21)11-4-2-3-5-13(11)18/h2-8H,9H2,1H3
+
+>  <PUBCHEM_NIST_INCHIKEY>
+ROYOYTLGDLIGBX-UHFFFAOYSA-N
+
+>  <PUBCHEM_XLOGP3>
+2.8
+
+>  <PUBCHEM_EXACT_MASS>
+302.062219
+
+>  <PUBCHEM_MOLECULAR_FORMULA>
+C16H12ClFN2O
+
+>  <PUBCHEM_MOLECULAR_WEIGHT>
+302.730683
+
+>  <PUBCHEM_OPENEYE_CAN_SMILES>
+CN1C(=O)CN=C(C2=C1C=CC(=C2)Cl)C3=CC=CC=C3F
+
+>  <PUBCHEM_OPENEYE_ISO_SMILES>
+CN1C(=O)CN=C(C2=C1C=CC(=C2)Cl)C3=CC=CC=C3F
+
+>  <PUBCHEM_CACTVS_TPSA>
+32.7
+
+>  <PUBCHEM_MONOISOTOPIC_WEIGHT>
+302.062219
+
+>  <PUBCHEM_TOTAL_CHARGE>
+0
+
+>  <PUBCHEM_HEAVY_ATOM_COUNT>
+21
+
+>  <PUBCHEM_ATOM_DEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_ATOM_UDEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_BOND_DEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_BOND_UDEF_STEREO_COUNT>
+0
+
+>  <PUBCHEM_ISOTOPIC_ATOM_COUNT>
+0
+
+>  <PUBCHEM_COMPONENT_COUNT>
+1
+
+>  <PUBCHEM_CACTVS_TAUTO_COUNT>
+1
+
+>  <PUBCHEM_COORDINATE_TYPE>
+1
+5
+255
+
+>  <PUBCHEM_BONDANNOTATIONS>
+10  17  8
+10  18  8
+12  15  8
+13  16  8
+15  16  8
+17  19  8
+18  20  8
+19  21  8
+20  21  8
+6  12  8
+6  7  8
+7  13  8
+
+>  <RULE5>
+1
+
+$$$$
+